I doubt you will regret the purchase.. I have a first gen nano and its great.. the big differences between the two generations is that the second generation has a 24hr battery and the first gen has a 14hr battery.. another difference is the case. the first gen has a shiny back and the second gen has no shiny back. the weight and size is a bit different also. The first gen is 3.5 x 1.6 x 0.27 inches the second gen is 3.5 x 1.6 x 0.26 inches. the weight of the first gen is 1.5 ounces and the second gen is 1.41 ounces.